Treatment of 5,13-di-tert-butyl-8,16-dimethyl[2.2]metacyclophane 1 with 1,3-dibromo-5,5-dimethylhydantoin (DBMH) in CH2Cl2 led to the first successful introduction of bromine onto the bridged methylene group.
Medium-sized Cyclophanes. part 69: YamatoT., HironakaT., and MiyamotoS., J. Chem. Res., 2006, 393.
2.
(a) Cyclophanes (Eds.: KeehnP.M., and RosenfieldS.M.), Academic Press, New York, 1983, vol. 1, chapter 6, p. 428; (b) F. Vögtle, Cyclophane-Chemistry, Wiley, Chichester, 1993.
3.
(a) BrownC.J., J. Chem. Soc., 1953, 3278; (b) N.L. Allinger, B.J. Gordon, H.-E. Hu and R.A. Ford, J. Org. Chem., 1967, 32, 2272.
4.
(a) SatoT., and NishiyamaK., J. Chem. Soc., Chem. Comm., 1973, 220; (b) T. Sato, K. Nishiyama, S. Shimada and K. Hata, Bull. Chem. Soc. Jap., 1971, 44, 2858; (c) S. Hayashi and T. Sato, Bull. Chem. Soc. Jap., 1972, 45, 2360.
5.
(a) TashiroM., YamatoT., and KobayashiK., J. Org. Chem., 1984, 49, 3380; (b) T. Yamato, J. Matsumoto, T. Ando, K. Tokuhisa and M. Tashiro, J. Chem. Res.(S), 1991, 276.
6.
YamatoT., FujitaK., MimuraK., and TashiroM., J. Chem. Res. (S), 2001, 351; (M), 2001, 910.
